Water → HCID 67398980, compound

HRID 70635Notes

Reaction equation

HRID 70635 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([O:28][CH3:29])[N:22]=2)=[CH:14]\[C@@H:15]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:30]I.O>O1CCCC1.C(OCC)(=O)C>[C:3]([C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([O:28][CH3:29])[N:22]=2)=[CH:14]\[C@@H:15]2[N:19]([CH3:30])[C:18](=[O:20])[CH2:17][CH2:16]2)=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67399368(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

Product 1

HCID 67398980HCID 67398980, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride (27 mg) was added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (185 mg) in tetrahydrofuran (5 mL), and the mixture was stirred at room temperature for 20 minutes. Methyl iodide (60 μL) was then added and the mixture was stirred at room temperature for 4.5 hours. Water and ethyl acetate were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=80:20) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]-1-methylpyrrolidin-2-one as a colorless powder (180 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 4.5 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationafter which the filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-ccebb00b75bf4388afd8aa6980727748
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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